Application of DMF—Methyl Sulfate Adduct in the Regioselective Synthesis of 3‐Acylated Indolizines.

Abstract

Fused pyridine derivatives R 0450 Application of DMF-Methyl Sulfate Adduct in the Regioselective Synthesis of 3-Acylated Indolizines. -The inexpensive adduct (III) is used for the synthesis of a broad spectrum of pharmacologicaaly interesting indolizine structures. -(PRZEWLOKA, T.; CHEN, S.; XIA, Z.; LI, H.; ZHANG, S.; CHIMMANAMADA, D.; KOSTIK, E.; JAMES, D.; KOYA, K.; SUN*, L.; Tetrahedron Lett. 48 (2007) 33, 5739-5742; Synta Pharm. Corp., Lexington, MA 02421, USA; Eng.) -Mais 48-136

Potential inhibitory effect of indolizine derivatives on the two enzymes: nicotinamide phosphoribosyltransferase and beta lactamase, a molecular dynamics study

“…Indolizines are an important group of compounds also because of their behavior as histamine H3 receptor antagonists, 5-HT3 receptor antagonists, and antitumorals [ 5 ]. In nature they have been isolated from animals, insects, plants, marine organisms, and microbes [ 6 ].…”

Indolizine Studies, Part 5: Indolizine-2-carboxamides as Potential HIV-1 Protease Inhibitors[1]

“…The indolizine-2-carboxylic acids 8a-c and CDI were each dissolved in dry DMF (with pyridine for reactions involving salts), and the resulting mixtures were heated at 40 C for 5 min. After cooling to room temperature, the amino compound (12)(13)(14)(15)(16)(17)(18) or their hydrochloride salts) was added, and the mixture was stirred overnight at room temperature (Scheme 3). Purification of the crude products was achieved using preparative layer chromatography to afford the corresponding indolizine-2-carboxamide derivatives 19-25 in 64-97% yield ( Table 1).…”

“…Indolizine derivatives have been reported to exhibit valuable biological activity as potential calcium entry blockers, [8] cardiovascular agents, [8,9] anti-5-hydroxytryptamine, [10] antihistamine, [10] antitumor, [11] anti-Mycobacterium tuberculosis (TB), [12] anticancer, [8,13] and anti-HIV [8,14] agents. Various approaches have been developed for the synthesis of indolizine derivatives.…”

Synthesis and SAR of Benzisothiazole- and Indolizine-β-d-glucopyranoside Inhibitors of SGLT2

“…As shown in Scheme 3, the indolizine intermediates 19k-o were prepared in two steps from 3-bromopicoline 17. Compound 19,20 The ketones 19k-o were reduced to diarylmethanes 12k-o using sodium borohydride with aluminum chloride.…”

“…As shown in Scheme , the indolizine intermediates 19k − o were prepared in two steps from 3-bromopicoline 17 . Compound 17 was treated with commercially available bromoacetophenones to afford picolinium salts 18k − o , which were treated with dimethylsulfate-DMF to provide ketones 19k − o . , The ketones 19k − o were reduced to diarylmethanes 12k − o using sodium borohydride with aluminum chloride.…”